The First Timers Club Pt. 05

"Don't know how many times I have to tell you this, Courtney, but that's none of your business," I said, but Kayla's reaction might as well have been a flashing neon sign.

"You did, didn't you?" Courtney pressed. "That's what you didn't tell us at brunch."

"Courtney!" I yelled, and she whipped her head around.

"What?" she snapped back.

"What the fuck is wrong with you?" I asked, raising my voice, and she backed down.

"Fuck, man. I'm just asking," she said lamely.

I stood up. "We agreed this would be a no judgment, no shaming sanctuary, didn't we?" I bore down on her with my glare. "Didn't we?" I asked again more forcefully when she didn't answer the first time.

She looked away and said, "Yeah," and I detected enough contrition to be satisfied she really did understand. I softened my expression.

"Sex is sex, guys, and if it feels good, and everyone's consenting, then there's nothing wrong with it. I know tons of women who love anal sex, even prefer it to vaginal. I know some women who can only have an orgasm from anal. I mean, Jesus fucking Christ, there's an entire sexual orientation that's practically perfected the art of anal sex."

Kayla glared at Courtney. "Yes, I asked him to put his cock in my ass," she confessed defiantly, "and I loved it, okay? Is that alright with you, Courtney?"

Courtney reacted to her name being spoken as a curse word with a sheepish shrug. "Yeah, cool. Whatever, Kiki. Good for you...I guess."

I sat back down. Brittney had watched the exchange like a tennis match, moving her eyes back and forth between the participants, and I'd temporarily forgotten the question to her which had sparked it, but she had not.

"I like it when the girl is tied up," she said quietly, and I turned to face her.

"Yeah? I like that too. What do you like about it?" I asked, silently praying that Courtney had learned her lesson and would keep her mouth shut this time which, thankfully, she did.

Brittney looked around and, sensing a more progressive audience, opened up a little. "I'm not sure. Maybe the way they just get...used?" She'd intonated it as a question, not a comment, and looked around to see how the others would react, but everyone held their tongues.

"By the way, if you guys agree with her, feel free to say so," I said, hoping to spur a more affirming dialogue, but no one took the bait. To Brittney, I said, "I love being tied up too sometimes, and the way a woman uses me to get herself off, it really excites me."

"Really?" she asked, as if I'd said something she desperately wanted to believe.

"Really. And I love it the other way around too. Controlling a woman, fucking her hard, pulling her hair, spanking her, choking her, calling her names. Some women really love to be used and degraded like that, you know? To varying degrees, of course, but I'm always happy to accommodate that. If they want it."

All four of them shifted in their seats as I spoke, and Brittney's face and chest grew increasingly flushed with every word.

"Is that something you'd like to try?" I asked, and Brittney's eyes bounced off Courtney before settling back on me.

"I don't know," she said, but I suspected she did know.

I moved to sit next to her and she stared at me with large emerald eyes, looking decidedly nervous. Moving slowly, I placed my hand on the side of her face, and she flashed a weak smile when I slipped it around to the back of her head, combing my fingers through her hair. Then I gripped a fistful and squeezed, not too hard but enough that she flinched.

"Do you like it when I pull your hair like this?" I asked.

Brittney swallowed hard and said, "Yeah," in a shuddering voice.

I put my other hand on her thigh, just beneath the cuff of her shorts, and slid between her legs. Her breath caught in her throat when I gripped the inside of her thigh near her crotch and squeezed.

"And do you like it when I grab you like this?"

"Y-yes," she hissed softly.

I leaned in to put my lips next to her ear. "Do you have your tampon in?" I asked, and she nodded. "Well, what are you waiting for? Go take it out so I can fuck you."

I pulled my head back and she looked at me and started to rise, but I held her and whispered, "You better not have any fucking clothes on when you come out of there. Do you understand?"

"Yes."

"Good. Get your ass moving."

I released her and, after another moment's hesitation to make sure I'd been serious, hurried off to the bathroom. I stood, my cock hard as a rock, and paced a little, taking deep breaths through my nose, preparing myself. I turned to the other three girls.

"Listen," I said to them, keeping my voice low, "You're going to see some things that might disturb you, okay? You might hear me say things that sound harsh, and Brittney might even scream and cry, but I promise you I'm not going to hurt her. Whatever happens, please just remain quiet and don't try to interfere. You'll just end up spoiling it for her and she's going to be mad at you for it."

"Dude, what the fuck are you planning to do to her?" Courtney asked, drawing her feet up underneath her legs, as if to protect herself.

"I'm serious, Courtney. If things get too disturbing for you, just leave, okay? Also, there's probably going to be a lot of blood."

"Blood? Why would there be blood?" Ashley asked alarmed, but I held up my hand.

"Period blood. She's on her period. If her flow is heavy, you're definitely going to see it. Don't worry, though, it's painless. It's just messy. Listen, bottom line: if it gets too intense for you, just leave, okay?"

They stared at me, their fragile trust in me stretched to its absolute limit, but one by one they agreed.

I straightened my back and held my arms to my side, closing and opening my fists, breathing heavily. Something primal surged within me. I caught Kayla's attention.

"You ready to watch me fuck your friend, baby girl?"

Her lips parted and she nodded.

"Good," I said in a low voice, shifting my gaze to the bathroom door. "Because I'm going to fuck the shit out of her."

When Brittney emerged from the bathroom, timid and uncertain, I gave her no time to think. I pointed to a spot in front of me.

"Get over here."

I said it neither harshly nor menacingly, but calmly and in a low, authoritative voice. One that told her compliance was mandatory. She moved quickly to the spot and, once again, I was struck by her long limbs and naked form and the impressive frame upon which they hanged. She looked like a Gaelic Amazonian.

As she arrived, I stepped forward, closing the distance quickly. I put my hand on her face and leaned in close, pressing my body against hers to stand cheek the cheek.

"Are you ready for this?" I asked in a soft whisper only she could hear, and she nodded slowly. "Say, 'Yes, I'm ready.'"

"Yes, I'm ready," she said, trembling with fear and anticipation.

"I want you to listen very closely. If anything I do scares you or hurts you or just makes you uncomfortable, say, 'Too much' and I'll back off, okay? I won't stop, but I'll back off. What are you going to say?"

Brittney's trembling intensified and she stuttered out, "T-too much."

"That's right. If you don't like something I'm doing and you don't want me to do it again, say, 'Stop' and I'll stop doing it and won't do it again. What'll you say?"

"S-s-stop," she managed to get out, and it sounded almost like a cry.

"Good. Last thing. If you don't want to keep going, if you want it to end completely, say, 'I'm done' and we'll stop whatever we're doing immediately. Repeat it."

"I-I'm d-done," she whispered.

"Perfect. Too much, stop, I'm done. Got it? Good. Spread your feet apart. Do it now."

When she did, I reached for her pussy and sank my finger into her vagina. She let out a shocked cry, but I shooshed her and withdrew it, holding it up for her to see. A light coating of ochre menstrual blood covered it to the second knuckle. I brushed it over her bottom lip, and her diaphragm fluttered and she whimpered through her nose as I leaned in to kiss her. I used my tongue to lick the blood from her lip and then pulled my head back to look at her.

Brittney trembled so violently she could barely keep herself under control as stress hormones flooded her blood stream, cranking up her fight, flight, or fuck response to eleven.

"Get on your knees," I said.

She nearly collapsed as she went to the ground and ended up on her hip, but she collected herself and rose to her knees, settling on her haunches. My cock pointed straight at her face and she reached for it.

"Did I tell you to touch my cock?" I asked, and she froze with her hand held out in front of her. "Put your hand down. You don't move, you don't talk, you don't do a goddammed thing unless I tell you to do it. Understand?"

She dropped her hand into her lap and nodded, avoiding my gaze.

"Untie your ponytail."

Brittney looked at me to ascertain if she'd heard me correctly, then reached back and removed the two hair ties holding her ponytail in place. Her long, curly red hair spread across her entire back and she used her fingers to tease it out and give it some volume and lift. Her appearance instantly improved.

"I like your hair better this way. You look fucking sexy as hell. I want you to wear it like this whenever we're in this room. Understood?"

"Yes."

"Good." I reached out with both hands to run my fingers over her temples and over the top of her head, gathering up a large volume of her hair, then gripped it in my fist until I had her head firmly under my control. "Open your mouth."

She did, and I stuck my cock inside. Brittney closed her lips around it and started to move her head and lift her hand to grab it.

"Did I tell you to move?" I asked, and she stopped moving and lowered her hand again. "You don't listen so well, do you?" I asked, and when she didn't respond, I added, "That was a question."

She considered how to respond with my cock in her mouth and opted to shake her head a little bit.

"No, you don't, so I'll repeat myself and hopefully you get it this time. You don't move, you don't talk, you don't do a fucking thing unless I say. Think you can remember that?"

A small nod.

"Good. Now listen up, my little cocksucking whore, I'm going to fuck your mouth and the only thing I need you to do is make sure those cute little cocksucking lips of yours never leave my dick. Think you can handle that?"

Another small nod and a thin line of drool.

"Excellent," I said, and then proceeded to fuck Brittney's mouth.

My control over her intoxicated me, and I reminded myself that she was still a virgin, wholly inexperienced and highly suggestable. I would need to proceed with caution. The last thing I wanted to do was traumatize her during her first time and leave her with a scarring memory. But I also wanted to open her up and challenge her while making it enjoyable for her at the same time, so I took it slow, applying firm authority over her rather than raw brutality.

For her part, Brittney's uncontrollable trembling eased considerably as I moved my cock in and out of her wet mouth. She looked up at me and I thought I detected the hint of a smile lifting her cheeks. Good. So far, she had seemed eager to accept a small measure of domination. I decided to test her willingness to accept a little degradation too.

I pulled my cock out of her mouth and took it in my hand. Holding her chin, I dragged the broad head over her ruby red lips, then used it to lightly slap her cheeks.

"You really love sucking cock, don't you?" I asked her, rubbing it over her face. Damn, I'd done it again. Old habits. Whatever. She nodded anyway. "I want to hear you say it. Tell me how much you love sucking my big cock."

"I love it so much," she said quietly, her eyes locked to mine.

"Say, 'I love sucking your big cock.'"

"I love sucking your big cock."

"Yeah, you do, don't you. Probably as much as I love eating your little pussy, hmm? Are you my cocksucking little whore?"

She hesitated a beat but nodded when I rolled my cock over her lips again.

"Say, 'I'm your cocksucking little whore.'"

Her eyes moved to where her friends sat, and she wavered, too self-conscious and embarrassed to say something so degrading in front of them.

"What's the matter?" I asked, and she moved her eyes back to mine. "Are you too chickenshit to admit it? Don't look at them, look at me. Fuck those bitches and fuck what they think. Be honest. Surrender to yourself, Brittney. You love sucking my cock, don't you?"

She nodded vigorously.

"And you want me to stick it back in your mouth and fuck you with it, don't you?"

Her eyebrows moved apart and she nodded again.

"Then stop hesitating. Just fucking say it. Say, 'I'm your cocksucking little whore' and I'll do it. I'll put my big cock back inside your mouth and fuck you with it."

"I'm your cocksucking little whore," she whispered, and I put my cock back inside her mouth and fucked her with it.

Brittney made desperate little noises as my cock slid in and out of her mouth, whines and mewls that drove me wild. She hungered for it and surrendered herself to my control. I found it difficult to restrain myself, to not go too fast or push too deep, to stay mindful that this wasn't about me. This was about Brittney and helping her to explore the boundaries of her desires. Despite the rational understanding of my responsibility, however, I couldn't help but test her limits even more.

"Oh, fuck yes," I muttered under my breath. "That feels so good. Mm, yeah, suck that fat cock you little whore." The degrading words drew her eyebrows apart and she whined again. I pulled out of her mouth and lifted her up by her hair. "Stand up."

She rose to her feet, and it felt strange to have to lift my eyes to look at her. I grabbed her throat, not squeezing, just holding it, and stepped closer. My cock slid between her thighs and the head pressed against the bottom of her pussy. Her mouth came open and I put my lips to hers and kissed her.

Brittney snaked her hand around my waist to grab my ass and pull me toward her, moving her hips against me and urging me to do the same. I pulled my lips away and she stopped.

"Did I tell you to move?"

She shook her head. "N-no," she said quietly and dropped her hand back to her side. "I-I'm s-sorry. I'm just so nervous and I want you s-so bad."

I favored her with an understanding smile and slid my hand around her waist to pull her against me. The movement caused her to bounce off me and my cock head to drag against her pussy. Her mouth opened and I felt her breath catch in her throat.

"I know, but you need to do what I tell you to do. Do you understand?" I asked as I pulled her toward me again.

"Yes."

I pushed on her back repeatedly, her belly bouncing softly against mine as my cock teased her pussy.

"I'm going to use you, Brittney. I'm going to use your holes to get myself off. You're going to suck my cock and I'm going to fuck your pussy and I'm not going to be gentle, okay? I'm going to fuck you hard and fast. I'm going to pound your little pussy with my big cock until you scream and beg me to stop, and then I'm going to fuck you some more."

"Oh god," she breathed as the speed and friction of my cock rubbing against her pussy increased.

"Do you want me to fuck you, Brittney?"

"Yes," she cried, nearly sobbing the word.

"Tell me you want me to fuck you."

"I do. I want you to fuck me."

"I don't want you to hold anything back. This is your chance. If I do something you like, something that feels good, I want you to tell me and ask for more. If you want me to do something to you, ask for it, beg me for it, and I'll do it. I'll fuck you any way you want, but you have to ask me for it. I'll make you feel so fucking good Brittney, but you have to give yourself to me. Can you do that? Can you be my little slut?"

Her urgent response flowed out of her in a stream of words. "Yes! God, yes. I won't hold back. I swear I won't hold back. I'll do it. I'll be your slut."

"Then get down on your hands and knees and show me your pussy so I can fuck you like the little slut bitch you are."

Brittney moved quickly, going to the ground and turning her backside to face me. Her long red hair spilled over her back and reached to the floor. I stared at her tiny pink asshole and the pink pussy beneath it. Her lips were swollen, engorged and opened, ready to receive me. I lowered myself behind her and lined up my cock, dragging the large head between her plump labia and the slick channel between them. She was thoroughly aroused, her secretions mixing with her menstrual blood to form a rouge lubricant that seeped out of her and coated my glans. I steadied myself with a calming breath.

Careful. Do not fuck this up. Take it slow.

I gripped her hip and pressed my cock against her pussy, and gently coaxed her back. "Take me inside, Brittney. Push back and take my cock into your pussy."

She didn't hesitate. She pushed against me and I watched her open to accept my girth. Slowly, the domed tip of my cock disappeared inside of her until the walls of her vagina closed in around it and the pressure increased. She was incredibly tight, but not quite as tight as Kayla or Ashley had been. Eager for me to be inside of her, I had to hold her back to slow her advance. Very gradually, my cock slid into the warm, slick envelope of her pussy.

"Nice and slow. Relax your pussy, okay? You're doing great. Let my cock open you up. Oh, fuck..."

Although incredibly slow to happen, Brittney took my entire length in a single try without stopping and the sensation was excruciatingly satisfying. When her soft ass pressed against my pelvis, I held her still against me.

"I'm in. I'm all the way inside you. How do you feel?" I asked, stroking her back. She trembled, small shivers that coursed through her body.

"I can feel you inside me," she said, her words choked. "It's..." She trailed off, unable to find the words to express how she felt. Then she sniffled, and I realized she was crying.

"Am I hurting you?"

"No," she said quickly, and sniffled again, trying to collect herself. "No, it feels...wonderful. I'm s-sorry. I know I shouldn't be crying right now, but I can't help it."

Thank god. I took another deep breath. "It's okay. Don't be sorry. Just try to relax. Feel me inside you."

After a few moments, she sniffled one last time and lifted her head.

"Are you ready?" I asked.

"Y-yes."

"Good. I want you to start fucking me. I'll guide you, but I want you to rock back and forth on your knees."

Brittney moved forward, and my cock withdrew from her pussy in a scene of horrific gore. Bright red blood coated my cock. Ashley gasped and covered her mouth, but I shot her a look and shook my head adamantly. No! Then, just as quickly as I'd been unsheathed, Brittney came back to take me inside.

"That's it. Just like that. Keep fucking me. Tell me how it feels."

"It feels...," and then she sobbed again.

I closed my eyes and cursed silently. Yes, I wanted her to explore her feelings and allow the moment to wash over her and overwhelm her emotions, but I couldn't help how that made me feel. I deeply regretted that I would be her first. She should have been with someone who loved her and cared for her as much as she did for them. Someone who would look into her eyes as they shared that first life-changing moment together. Instead, I'd told her to bend over in front of me so I could fuck her like an animal, and I wasn't sure if I could feel worse about myself.

You're not her boyfriend. She asked you for this, so don't fuck it up for her.

I shook my head to clear the negative thoughts. To stop now would only humiliate her. For better or worse, I was her first, and if I couldn't be the gentle love of her life who would cuddle with her long after they'd consummated their relationship, I could at least give her an experience of carnal savagery that she'd remember for the rest of her life.